2-(Hydroxymethyl)-4-iodophenol → 5-Iodosalicylaldehyde

HRID 650147

反応式

HRID 650147 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5]>CC(C)=O.[O-2].[Mn+4].[O-2]>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5]

参加物

4

反応物 1

HCID 125452592-(Hydroxymethyl)-4-iodophenol

生成物 1

HCID 2526125-Iodosalicylaldehyde収率 58%

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 180Acetone溶媒

実験手順

To a stirred solution of 2-hydroxy-5-iodobenzyl alcohol (43.5 g, 174.0 mmol) in acetone (700 mL) was added 85% activated manganese(IV) oxide (5 micron, 50 g, 494.0 mmol) and the solution stirred at room temperature for 16 hours. The manganese oxide was removed by filtration through diatomaceous earth and the filtrate concentrated in vacuo. The product was purified by flash silica chromatography (0-20% ethyl acetate in hexanes) The 2-hydroxy-5-iodobenzaldehyde was obtained as a greenish-yellow solid (24.3 g, 58%). A small amount of the 2-hydroxy-5-iodobenzaldehyde was recrystallized from methanol/water to afford an analytical sample and the remainder of the compound was used without further purification: mp 99-101° C. 1H NMR (CDCl3/300 MHz) 9.83 (s, 1H), 7.79 (d, 1H, J=2.2 Hz), 7.77 (dd, 1H, J=8.7 Hz, J=2.2 Hz), 6.81 (d, 1H, J=8.7 Hz). ESHRMS 246.9229 (M−H Calc'd 246.9256).

後処理

  1. customThe manganese oxide was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe product was purified by flash silica chromatography (0-20% ethyl acetate in hexanes) The 2-hydroxy-5-iodobenzaldehyde

出典と根拠

ORDレコード
ord-d75218f50aa0470e9e4004ba7f96150e
出典データセット
uspto-grants-2001_08
特許番号
US06271253B1

関連ノート

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